Head over Feet

Morissette and Ballard wrote it and Ballard produced it. It was released on 22 July 1996 as the album's fifth single outside the United States. It is a gentler song than the earlier singles, about a couple who are best friends as well as lovers, and the narrator thanks her friend for his patience and devotion. Its lyric "best friend with benefits" is the earliest known use of the term friend with benefits. The sheet music is in C major, with the chorus in D major, at 120 beats per minute.

In Canada it spent eight weeks at number one on the RPM chart, the longest run of her four number ones from the album. It was her first number one on the Billboard Adult Top 40 chart, and it topped the Top 40 Mainstream chart too. In the UK it reached number seven and was her first top-10 single there. A live version appears on Alanis Unplugged (1999), and she re-recorded it acoustically in 2005. At Glastonbury in 2025 it featured a harmonica solo. It was one of three Jagged Little Pill songs that the TV series Glee paired with Carole King songs in 2015, this one with Will You Love Me Tomorrow.